K.H.
If you're looking to save money consider renting a breast pump. And depending on how motivated you are, consider buying a used one. Some people may be grossed out, but you buy new all the parts connected to your body so it's sterile.
In my experience, breast pumps last a very long time, so buying used is a good deal. I have mom friends who have rotated a breast pump around families for over a decade and it still works like a charm. My breast pump works great, has had at least 3 owners and is probably about 7 years old.
As far as when to pump and feed breast milk, I guess it doesn't matter. Only keep in mind to regularly pump throughout the day (and night) to keep your supply strong.